Solvent-free microwave synthesis of novel 6-hydroxypyrimidin-4(1H)-one derivatives using arylmalonates

doi:10.1016/j.tetlet.2007.08.134

Tetrahedron Letters

Volume 48, Issue 46, 12 November 2007, Pages 8250-8252

https://doi.org/10.1016/j.tetlet.2007.08.134 Get rights and content

Abstract

The disclosure herein describes the rapid synthesis of novel 6-hydroxypyrimidin-4(1H)-one derivatives via a solvent-free microwave cyclocondensation reaction using di-(2,4,6-trichlorophenyl)malonates and a variety of heterocyclic amines.

Graphical abstract

Section snippets

Acknowledgments

The authors would like to acknowledge Christopher J. Dinsmore, Mark T. Goulet, and Ben Munoz for their helpful suggestions in the preparation of the manuscript.

References and notes (9)

A. Rivkin et al.
Bioorg. Med. Chem. Lett.
(2006)
M.X. Xu et al.
Yaoxue Xuebao
(1995)
W. Duan et al.
Zhongguo Yaowu Huaxue Zazhi
(1995)
M.H. Sherlock et al.
J. Med. Chem.
(1988)
L.A. McQuaid et al.
J. Med. Chem.
(1992)
M. Rowley et al.
J. Med. Chem.
(1997)

There are more references available in the full text version of this article.

Cited by (13)

Cascade Wolff Rearrangement and Double N-Acylation: A Cyclization of α-Diazoketones with 2-aminopyridines or 3-aminopyrazoles to Synthesize Fused Pyrimidinediones
2023, Advanced Synthesis and Catalysis
A cascade Wolff rearrangement and double N‐acylation reaction has been developed for the synthesis of fused pyrimidinediones in one‐pot under air. These reactions were performed with α‐diazoketones and 2‐aminopyridines or 3‐aminopyrazoles under catalyst‐ and additive‐free conditions. The protocol avoided traditional purification procedures, such as organic solvent extraction and column chromatography. The synthesis of biologically active molecules and gram‐scale experiment demonstrated the potential applications of this reaction.
A green and effective route leading to antiradical agents with 3-arylmethyl 4-hydroxyquinolin-2(1H)-one moiety
2022, Tetrahedron Letters
Citation Excerpt :
Silver-catalysed cyclization is developed to synthesize the target compounds 1 from o-propragyl anilines 6 with the insertion of carbon dioxide [9]. Cu(I) [10] and Pd(0) [11] catalysed reactions are routes starting with o-bromobenzoate 7 and amide 8. A logical route leading to 3-substituted 4-hydroxyquinolin-2(1H)-ones 1 would be alkylation of unsubstituted 4-hydroxyquinolin-2(1H)-one 9: however, all efforts usually expires with 3,3-disubstituted product 10 and additional dealkylation step is required [12].
A new, green, convenient, cost- and atom effective route leading to 3-arylmethyl 4-hydroxyquinolin-2(1H)-ones from arylaldehydes and 1,3-dicarbonyl compounds in triethyl ammonium formate in good to excellent yield is presented. The provided method foresees the Knoevenagel condensation between a 4-hydroxyquinolin-2(1H)-one and an aromatic aldehyde followed by in situ trapping of the arylidene intermediate with the hydride ion. All synthesized compounds were tested for their antiradical activity against DPPH and GO free radicals. The antiradical activity of the 3-arylmethyl 4-hydroxyquinolin-2(1H)-ones was comparable to or even higher than that of some commercially widely used antioxidants like BHT, TBHQ, or α-tocopherol.
Chapter 6.1: Six-membered ring systems: pyridine and benzo derivatives
2009, Progress in Heterocyclic Chemistry
Citation Excerpt :
Elneairy et al. reported the syntheses of a 1H-pyrazolo[3,4-b]pyridine and thieno[2,3-b]pyridines from a 2-hydrazinopyridine derivative and 3-cyanopyridin-2-ylthioacetate derivatives, respectively <07PS1351>. Many novel preparations of fused heterocyclic systems from 2-aminopyridine derivatives were also divulged <07JHC145; 07T8157; 07TL5039; 07TL5535; 07TL8250; 07TL8943>. Pyridine N-oxides and pyridinium salts constitute an interesting class of pyridines that possess unique physical properties and chemical reactivity.
This chapter provides an overview of six-membered ring systems, including pyridine and benzo derivatives. Pyridine derivatives are important heterocyclic systems whose preparation, reactivity, and properties are of continuing interest. The biological activity associated with naturally occurring and synthetic pyridines has led to the development of pyridine-containing medicinal scaffolds and investigations into their pharmacological properties. This chapter presents a summary of the methods developed for the syntheses and reactions of pyridines, quinolines, isoquinolines, and piperidines. Cyclocondensations and related polar cyclizations are the most widely used methods for preparing pyridines, dihydropyridines, and dihydropyridinones. Efforts have been directed towards utilizing multicomponent cyclocondensation reactions as one-pot procedures to conveniently synthesize a variety of pyridine derivatives in an efficient manner. In addition, much attention has been focused on improving efficiency with the incorporation of microwave technology and developing more environmentally friendly protocols. The Hantzsch synthesis of pyridine is a cyclocondensation method of considerable importance. This route classically involves the condensation of four components, including two molecules of β-carbonyl compounds, an aldehyde, and ammonia (or an equivalent) to form 1,4-dihydropyridines, which can be aromatized into pyridines.
A novel strategy for the synthesis of uracil derivatives using bis(pentafluorophenyl)imidodicarbonate
2008, Tetrahedron Letters
On the hydrolysis of diethyl 2-(perfluorophenyl)malonate
2020, Beilstein Journal of Organic Chemistry
Metal and Solvent-Free Synthesis of 2H-Pyrido[1,2-a]pyrimidin-2-ones Catalyzed by Elemental Sulfur
2019, European Journal of Organic Chemistry

View all citing articles on Scopus

View full text

Published by Elsevier Ltd.

Solvent-free microwave synthesis of novel 6-hydroxypyrimidin-4(1H)-one derivatives using arylmalonates

Abstract

Graphical abstract

Section snippets

Acknowledgments

Bioorg. Med. Chem. Lett.

Yaoxue Xuebao

Zhongguo Yaowu Huaxue Zazhi

J. Med. Chem.

J. Med. Chem.

J. Med. Chem.